Misery and Happiness
by osirisapollo
Summary: Ever since his stint as a human, Castiel has been cursed with all kinds of feelings he's not used to. Even the return of his grace hasn't rid him of the annoying things. He decides to research what they all mean, and does not like what he finds. A Sastiel get together fic
1. Research

Castiel knew he'd been acting weird, but he had no idea how to stop it. He knew every day that passed with him acting this way caused the Winchesters to look at him more and more oddly. They had questions,and they probably wouldn't wait much longer before they started asking them. He also knew he had no answers to give them.

He started with research. The brothers always started with research, and he had come to trust their judgement. He was already filled with plenty of knowledge, but had yet to acquire the knowledge he needed to understand these new feelings he had gained during his stint as a human. The emotions he hadn't been able to brush off, even after he had his grace restored.

It had taken much more effort than he'd thought it would to discover the correct combination of words to describe what he was feeling. Once he had, it had only made everything worse.

When he'd found the word infatuation, it seemed to fit. He was infatuated. That was why he acted so strangely. It also helped to explain why he could act normally whenever he was away from the Winchesters, but not when in their presence.

It was inconvenient, and unexpected, but not wholly surprising. He knew the Winchesters were considered to be very good looking men, and it stood to reason that he'd noticed such a thing while he was human. He certainly wasn't the first human that had made that observation. All of the ingredients for affection were there: the large amount of respect he held for the brothers, and the significant amounts of time he spent with them. It seemed entirely understandable that his human emotions would choose them to latch onto.

Somewhat pleased with this explanation, and knowing that these feelings tended to be short lived, he breathed a sigh of relief. Yes, he was still suffering the effects of humanity, but he would be fine, eventually. He could ignore these feelings until they went away.

It wasn't long after defining his infatuation that he experienced physical attraction, and with it a physical response he was unprepared for.

The first time it happened he'd been so surprised he nearly dropped the pile of boxes he'd been carrying. His body's response, coupled with the knowledge that he could develop more feelings even with his grace restored, caused him to stumble. He was saved from further embarrassment when a strong hand was placed on his back, and another grabbed the top of the boxes to keep them from falling over.

"Take it easy there, Cas." Sam told him, making sure he was steady before releasing him. He was then graced with a sweet smile.

Castiel felt his face heat at the closeness of the youngest Winchester and the embarrassment of his near mishap. Sam's smile was accompanied by a pair of dimples and a soft warmth in his eyes, and that was not helping Castiel's situation.

"It's fine, Sam. I have it." He sounded breathless, even to his own ears, and the hunter narrowed his eyes.

"Are you feeling alright?"

Castiel nodded and took a step away from the other man, needing the distance. He'd forgotten what had caused his reaction in the first place, and was immediately reminded. His step back only gave him a better view of the youngest Winchester, and his current shirtless state. He felt his face heating again and averted his eyes quickly.

"Yes. I'm fine." He lied, and forced his feet to carry him out the door before he could do anything else foolish.

Therefore, Castiel had to do more research, and was relieved to find that sexual attraction was another symptom of infatuation. He would have to wait out that feeling, too. Although, it tended to be much harder to ignore (no pun intended).

It wasn't until a few weeks had passed that the angel realized he may have misdiagnosed his problem. Instead of fading, his affection for Sam became even more consuming. It seemed that every move the man made was arousing. Everything he said was endearing. When he was upset, Castiel wanted to go to the ends of the Earth to fix it. When he was happy, it inexplicably cheered the angel as well.

Worst of all was when he smiled. The angel couldn't contain his body's reactions to Sam's smile. All of the feelings he'd spent his days pushing down came bubbling up, and he found himself enveloped in an ever increasing mix of emotions he'd yet to find definitions for.

More research was in order, and the results he found unsettled him greatly. Apparently, this combination of happiness and misery had a name. A name he'd heard many times before, but had never experienced for himself. An emotion that may have been able to fade, given time and distance, but would never really go away.

Love.

Castiel had fallen. He had rebelled against heaven, and their plans, too many times. He'd lost his grace, and been human. Then, he had proceeded to do the worst thing imaginable. He had fallen in love. He really had fallen in every possible way.

He looked for another way out. He spent quite a few nights searching frantically through books and the internet, for any information on the subject he could find, but they all said the same. Love could fade, but it would never be gone. Not that it mattered, because Castiel didn't have the time and wouldn't be able to keep the distance it would take to dissipate.

He was among the Winchesters almost continuously. They had been fighting alongside each other for so long now, and he couldn't imagine leaving. Everything he read said it could take years, and he didn't have years to spend away from them.

Then he came across another kind article, and then a few more like it. These were all about how to make someone love you back.

Intellectually, Castiel knew that angels were not meant to be with humans. He knew it was a terrible idea to try make anything come out of his weakness, but he also knew that he wanted it. He could only imagine what it would be like to have his feelings returned, but assumed it would be wonderful. Ignoring his feelings hadn't worked, and although he knew it was possibly the worst course of action he could take, he decided to try this new direction.

Most of the articles that he had read online seemed like utter nonsense. He had been observing humanity for a very long time, and of all the things he'd read, very few of the suggestions seemed legitimate. There were a few, though, and he would implement his plan as soon as he figured out exactly how to approach the man he was apparently in love with.

 **Focus on the ways you are alike:**

This idea seemed to have merit. In his observation of humanity common interests seemed to be the way that most humans were drawn to each other. They seemed to form little groups depending on what attracted their mutual attentions. The shared level of fascination with a subject could mean anything from seeing each other once a week to play a game, or even developing a much deeper relationship based on multiple commonalities.

It was clear to the angel that if he wanted Sam to realize how many interests they shared, he would have to find some that he didn't also share with Dean. All three of them could say they shared an interest in humanity. They all wanted to protect humans from the evil things that roamed the earth. So, he decided to try to find something that only he and Sam shared.

His first thought was that they both seemed to enjoy researching. They were usually the ones that used their memories in combination with any information they could find to come up with a plan, while Dean tried to find a reason to not be involved. He'd thought it a good place to start and intended to use it as his first step.

The very next time they had a chance to research together, though, Sam had slammed a book shut and grumbled about how he hated researching. He then left the library so abruptly that Castiel doubted he would return. The angel resigned himself to doing the rest of the research alone.

Sam returned less than an hour later. He apologized profusely, pulling up a chair and popping open the book he had abandoned. "I just get frustrated when Dean abandons me with all the research sometimes. That doesn't mean I can do the same thing to you." He'd said. Castiel had just been grateful that he hadn't been left to do all the work. Sam thanked him for his continued help, and then spent the rest of the time working out a plan to make Dean do all the research on the next case.

Castiel wasn't positive, but the way Sam was talking made him think the hunter was less interested in research and maybe only felt obligated to do it. In that case, it wouldn't be a useful tool in the angel's efforts to find common interests. He would have to find another similarity between them to build on.

The next opportunity he had to be alone with the younger hunter, Castiel decided to try to find some other things they had in common. Dean had abandoned them in a shitty motel, intending to find a bar and drink until he could no longer remember the more disturbing aspects of their most recent case. Sam had never been the type to drink away the pain, so the angel decided to find out how he intended to deal with it.

"Here, I'll show you." Sam's smile had a hint of sadness that Castiel knew would be there for a while. It had been a tough case with a lot of casualties. The angel joined the hunter at the table, pulling his chair closer when the other man indicated that he would need to be able to see the screen of his laptop.

"It really depends on my mood, but watching funny movies usually helps. Sometimes I watch movies that are just supposed to make you feel good. Either way, it's usually completely mindless entertainment. If you really focus on the story, you can spend an hour and a half thinking and seeing funny things. It just takes your mind off of everything else for a while." Sam explained as he set his laptop between them on the table.

"I've never watched a movie before." Castiel admitted, although the admission was exactly the opposite direction that he'd originally intended the conversation to go in.

"Really? Yeah, I guess we haven't ever really gotten around to showing you the lazy side of being human." Sam sounded contemplative, and he shot the angel an apologetic grin.

"You'll like this though. It's called slapstick humor. You don't really have to understand a lot of references or anything. It's mostly just based on people doing dumb and embarrassing things."

The movie was indeed humorous. Castiel found it fairly easy to keep up with the nearly useless storyline, and was even amused into full laughter a few times. He felt bad for the people at first, but Sam made it clear that the whole purpose was to put characters into the oddest of situations for the enjoyment of the watchers. They weren't real people, they were characters, so there was no shame in laughing at their antics.

The greatest joy, though, had been hearing Sam's laughter. It wasn't something he'd had many chances to hear, and he savored the opportunity. At the end of the movie Sam asked him if he liked it, and he answered in the affirmative, but he also worried that he was being dishonest. Did he enjoy the movie, or had his mood been improved by the hunter? He didn't know the answer for sure, and decided to research by watching another movie while the hunter was sleeping. He'd read that honesty was important in a relationship.

Sam set him up with a similar movie, before dropping into one of the beds to get some sleep. Luckily, Castiel had enjoyed that movie as well, and wouldn't have to take back his answer.

It was nearly another week before he was left alone with Sam again. They were thankfully in the bunker, so Castiel had his own space to retreat to when his affections overwhelmed him. He'd been hiding in his room more and more often as his emotions took a stronger hold on him. Each day he woke up a little more in love with Sam Winchester, and each time he thought about doing something about it he became increasingly more nervous.

By the time he'd gathered the courage to try to point out similarities between them he'd just said the first thing that had come to his mind.

"The only person that has screwed things up more consistently than you, is me."**

He and Sam had so many things in common, and that was the one he chose to use. He was older than the calendars human's used to tell time, and he couldn't even control the words that came out of his mouth. Of all the things he wanted to say and all the ways they were alike that he'd thought of to help him form a bond with the youngest Winchester, somehow the one that was actually voiced was the worst of all his options.

He'd excused himself fairly quickly after that. He knew the admission had stunned the hunter, and he knew his abrupt departure hadn't helped. He could think of no way to fix what he'd said and he practically ran from the room to escape his own ridiculous words.

Castiel no longer searched for commonalities between them. Clearly he'd have to find a way to get to the younger Winchester that didn't require talking. He was obviously terrible at it.

 **The way to a man's heart is through his stomach:**

Castiel was sure that this one was true. Dean continuously told people he loved them when they brought him food. Although, it would likely be much harder to get Sam to do the same. He was much more picky about his food choices, and while Dean favored the comforting foods that could easily remind you of home, Sam was more concerned with his health. It would be very difficult to find something to bring him into his target's heart through his stomach.

The angel started again with research. He tried to find comfort foods that were healthy, but he could only find recipies. He was under no illusion that he would be any good at cooking, especially as he had no sense of taste. According to his reading, constantly tasting the food as you made it was essential to a good meal. He would have to think of something else.

His next step was to go to Dean for advice. He knew this step would be tricky, since the hunter had a way of making bad situations worse. He had no desire for Dean to know of his true intentions, though.

"Dean, when you were children, was there anything that you liked to eat?" His research said that many men liked to have things made for them that reminded them of their childhood.

"Uh… yeah, buddy. I liked to eat a lot of things." Dean already sounded suspicious which did not bode well for the rest of the conversation. Castiel pressed on anyway.

"Was there anything in particular that you and your brother enjoyed?" Even the angel was aware that these questions would seem odd, especially as he'd just popped into the library and interrupted whatever Dean was looking at.

"Dude, I don't know. Macaroni and cheese? What's with the food questions?" The hunter was beginning to look unsettled by the conversation, but his research specifically said 'and I don't mean macaroni and cheese' so the angel pressed on.

"Did your father ever make you something that you enjoyed on occasion?" The page he looked at had said mother, but he was well aware that hadn't been possible.

The hunter's eyebrows dipped and he looked a little angry now.

"My father didn't cook. He didn't have time for that stuff. I made what I could for me and Sammy. We didn't really eat like normal kids." Dean glared at him for a moment, but visibly tried to calm himself. "What's this all about, Cas?"

The angel felt guilty, finally realizing he was drudging up old memories that Dean didn't seem too pleased at having to think about. It hurt his heart when he thought about the hunter as a child trying to cook for his little brother, even though he was likely so young he should not have been allowed near the stove. The combination of what he knew to be guilt, and the new emotion that seemed to be causing him physical pain, also seemed to be pressing him to do something else. Something he had never really understood before.

Following his instincts, Castiel leaned down to wrap his arms around the hunter's neck. It was difficult with the positions they were in, and not very comfortable, but he had given into the urge to hug Dean.

"What is happening?" the hunter didn't seem to know what to do and he just froze in place while the angel tried to embrace him.

"I'm sorry." The angel took a step back to give the man some space, and the hunter visibly relaxed. "I was not thinking. I was reading about comfort foods, and it said they mostly came from your childhood. I didn't mean to upset you." That wasn't precisely the truth, but it was close enough.

Dean sighed. "It's alright, buddy. We don't really have anything like that. We ate a lot of fast food and really easy meals when we were kids."

"I understand." Another lead straight down the drain.


	2. Try Again

There was only one more suggestion from his research that seemed to have any merit. There was only one more chance that his limited knowledge on the subject might actually be helpful.

 **Reveal things about yourself:**

The first opportunity to share more about himself came when the brothers were digging through the biblical lore the Men of Letters had collected. Of course, all of the information in the bunker was from well before the apocalypse and mostly just speculation. The guidance for dealing with angels was severely lacking.

"Just write: Dicks with wings, avoid at all costs." Castiel heard Dean say. The angel was in the kitchen, but could easily hear the hunters in the other room.

"Unless the angel answers to Castiel." Sam added.

"In which case, stab him in the heart, so he can stare at you like you're a spec of dirt on his shoe." The eldest Winchester added. The comment was enough to convince the angel he should intervene, ensuring such information would not actually be placed in the files.

Sam's laughter carried down the hallway as Castiel headed in their direction. "I'd forgotten about that! I can't imagine how freaked out you must have been when he wasn't even bothered with a demon knife sticking out of his chest."

Castiel made his way into the room just in time to see Dean replaying the scene from when they first met. The hunter was indeed staring at Sam as if he was a particularly irritating inconvenience, but not something remarkable enough to be a threat. One of the knives had been taken off a display and was tucked under his arm to look as if he'd been stabbed. He glared at Sam threateningly for a moment before he pulled the knife out slowly, dropping it to the floor. The angel wondered if it had truly looked that dramatic when he'd done it.

"Insignificant human! You can not kill me with a demon knife! For I am an Angel of the Lord!"

The brothers laughed at the ridiculous reenactment while Castiel glanced between them. He didn't know if they were aware he'd come into the room.

"That's not quite the way I remember it." He said, if only to announce his presence.

"Yeah, cause you were the one doing all the scary shit!" Dean answered immediately.

So, they had known he was there. Which hopefully meant that they weren't making fun of him with their laughter.

"I was not trying to scare you. I honestly did not expect you to try to kill me when you summoned me."

Dean laughed at that. "You didn't know me then."

Castiel spared him a smile. "Yes, I know better now."

Dean grinned at that answer, obviously pleased with the insinuation of his reputation.

Castiel moved toward the brothers, ready to input into the conversation he'd overheard.

"Perhaps I might be of assistance in the effort to update the archives about angels?" He didn't wait for an affirmative answer, taking a seat at the table with Sam.

"Yeah, that would probably be pretty helpful. We mostly only know the things you've taught us anyway." The hunter admitted, throwing the angel one of his adorable smiles. He then placed his hands on the keyboard, as if prepared for a monologue he'd have to transcribe. "What do you think we should add?"

"Perhaps we can add the symbols needed to keep angels out and the banishing sigil to get rid of them if they do find a way in." Castiel could see how allowing mankind the option could backfire, but he also knew that the humans he'd entrusted the information with had used it sparingly so far.

"Yeah, that's good. Maybe we should add information about befriending angels…" The younger hunter was typing away as his brother made a face of disapproval. Castiel had to agree with that reluctance, although he hated it.

"I doubt there will ever be many angels that are sympathetic to the plights of humans." He told Sam gently, knowing that the hunter liked to see the best in everyone.

Sam glanced up from his laptop as if trying to gauge the seriousness of the angel's words.

The hunter seemed confused about the certainty that Castiel spoke with. "You don't think there are any others that understand the importance of free will?"

The angel was unable to disguise the disappointment in his voice. "I am an anomaly among my brethren. Even after proving that angels also possess free will, they are unlikely to change their views on the subject."

Although Sam looked unsettled at the way Castiel said that, it was the truth. Angels were made to do as they were told. Following orders was ingrained in them from the moment they'd been made, and the difficulty of escaping their roles was well documented if only in the incredibly small numbers that had chosen to do so.

Castiel was not ashamed of the role he had taken in the new order. He knew that helping the Winchester's stop the apocalypse had been the correct path for him. He was well aware that his current predicament was a result of that decision, but even so he could not feel that he had made the wrong choice. He would much rather be suffering the effects of humanity than cleaning up the devastation that would have preceded the war of good and evil.

"I guess you're just one of a kind then." Sam said, his dimples pronounced even as he looked down at the screen in front of him. Castiel couldn't see his smile, but he knew it was there.

The angel couldn't say he'd never had a similar thought about himself before. Although, when he did, he was always filled with a strange mixture of pride and shame at the fact. When Sam said it though, with the warmth in his voice and the smile on his face, it was clearly a compliment. Castiel could feel his face heating and a rush of emotion through his system. Sam seemed to think it was good that he was different.

"Yeah, our Cas is a rebel. I wouldn't have it any other way!" Dean patted him on the shoulder as he said it, making Castiel blush even further. He realized that such a word was also compliment when it came from Dean. "If my guardian angel was just a little bitch that told me to be good all the time, I don't know what I would have done."

The angel rolled his eyes as he corrected the hunter. "I am not your guardian angel." He made sure that he sounded sufficiently put out by the idea. The brothers shared a laugh at his tone.

Sam allowed them a moment of amusement before he spoke again. "From what I've read of what they already have here, it seems like even they knew that angels were not meant to sit on our shoulder and tell us to be good." The youngest Winchester was clearly trying to get them back on track.

"The lore mostly says that angels are 'messengers from God' and that they haven't been seen in some time. The only recorded sightings are from the bible, and the Men of Letters clearly thought that it was a reliable enough source to say that angels were probably real, but not a reliable enough source to say that it had to be truth. It sort of implies that the creatures recorded in the bible might have been something else completely. And that they had no definitive proof of whether the angels had been here or not. It's written as if they wanted to believe what the bible told them, but couldn't call it fact because there were no other records."

Sam turned a few pages of the book he'd placed next to his laptop. "It doesn't really speculate on what other kinds of creatures could have been posing as angels in the biblical stories, though. It goes on to question whether the men that identified themselves as angels were lying about their origins. This specifically states that they couldn't find any other recorded instances of angel sightings from that period, but that they didn't believe that angels would only visit those few men, if they had truly been around then."

"They were wise not to believe everything they read." Castiel nodded sagely at the choice.

Sam looked baffled as he met his eyes. "What does that mean?"

"The book was written by man, and as such is not wholly accurate. There are parts of the story that have been altered and some that were left out altogether." The angel was surprised by the shock that seemed to play across the other man's face.

"Are you saying that the Bible is inaccurate?" Sam's question seemed genuine, as if the existence of angels had been enough proof for him that the book was truthful.

"The testimonies of the bible have been altered many times. The men that recorded the events chose which parts to bring together for the book."

The look that the hunter graced him with was a cross of shock and intrigue that sent a tingle down Castiel's spine. "Like what?"

It was if Sam was finally playing along with one of his plans. The angel could feel a warmth spreading through him as excitement trickled down his spine. This plan might actually work. Sam was interested in the things he had to say.

"The most irritating to me, personally, is the book of Judas. It was altered just to make the apostles seem less afflicted by the less desirable of human emotions."

"Meaning what?" So now even Dean was interested in his story.

"Jesus asked Judas to kill him. He felt his spirit was trapped in his body and he wanted to return to heaven. Judas turned him in because he could not bring himself to do the deed himself. Of course, that part of the story couldn't be included in the book. They removed it when they rewrote the story of how Judas died."

"Wait, didn't Judas commit suicide?" Sam asked as if he didn't know if he was remembering the story correctly.

"That is the way the story was printed, but the other apostles killed Judas. They originally altered the story to say that Judas was killed in reaction to his betrayal, although their actions had much more to do with Jesus' clear favoritism of Judas. The writers would not allow Jesus' other apostles to look like they suffered from jealousy, which is a sinful emotion. By the time they printed the stories they had decided that the apostles should have had no hand at all in Judas' death. Murder is a sin, after all. Even a murder for revenge."

"Wow." Both of the Winchesters looked fascinated by the idea, and Castiel was quite proud of himself for finally finding a way to use one of his research suggestions to his advantage.

"There are actually many stories that didn't make it into the finished book. The church was content to only include the stories that went along with their own wants for humanity." He hoped that sharing a few more of his stories would help him in his plans.

"But if you guys were there, why didn't you make them include everything? If you guys knew what was happening, why didn't you stop them?" Sam asked him, instead. It wasn't the way he was hoping this would go, but he answered anyway. At least the hunter was able to recognize that this was a story he had witnessed in his lifetime.

"At the point that the book was being made, we were told we could no longer interfere. It was explained that we could no longer make contact with the humans, and any angel allowed on this plane was only here for observation. So, we could watch the humans rewrite the stories as they saw fit, but were not able to do anything to change it."

"Wow. That must have been hard."

The angel made an affirmative noise. It had been hard, but it was so long ago now that it no longer caused him pain. Some humans had learned valuable lessons from the book, no matter the falsities in it.

"It was a very important part of human history. I was one of the few angels that had been selected to observe humanity during the time." Castiel could not hide the pride in his voice as he'd said that, it was one of the few times he'd been observing when a large piece of history had been made.

"Jesus Christ, Cas! How old are you?" Dean exclaimed, un-ironically.

The angel recoiled immediately. Perhaps he hadn't thought through the consequences of sharing these stories with them. He did not truly want to remind Sam that he was considered a supernatural creature to them. It was one of the things he knew would make the other man less likely to want to pursue anything with him, if he ever got that far.

The younger hunter glared at his brother after witnessing Castiel's reaction to his outburst. "Dean, you are the most insensitive ass on the planet."

"What? How was I supposed to know that his age was a touchy subject?" The elder Winchester seemed baffled by the angel's response.

"No, it's fine. I know I am very old by human standards." Castiel wished he knew how to change the subject without being incredibly obvious about it. He was hoping to build a connection with the younger Winchester, not remind him that he was an incredibly old supernatural being.

"Sometimes I forget that you're an angel." Sam said softly, although they had been working through angelic lore only minutes before.

"Does that bother you?" The angel couldn't help but ask.

The hunter wore a perplexed expression. "Why would it bother me?"

There was no way to answer that question without being too obvious. No way to reword his own to get the information he needed without saying too much. Castiel truly wanted to know if Sam would be bothered by the fact that he was an angel, if the time ever came that he had the courage to do something with his feelings. One of many things he worried about since he'd decided to pursue his feelings for the human. He knew that Sam had a relationship with the demon that was shaping him to be Lucifer's vessel, but he worried the experience had taught the younger Winchester a lesson in trusting supernatural beings. In which case the hunter would likely not be interested in becoming involved with an angel either. He changed the subject, bringing the conversation back to angelic lore.

He had finally gotten around to doing one of the suggestions correctly, but instead of worming his way into the heart of his beloved, he'd reminded him of how much older he was. Instead of making steps toward romance, he'd reminded Sam that he was one of those untrustworthy supernatural creatures that the Winchesters spent their days hunting. He was terrible at this.

After his last failed attempt, Castiel decided that it might be best to go back to ignoring his feelings. All his plans to convince Sam to love him were failing before he even got the chance to implement them. He hoped it would be easier if he stopped thinking about it, so he decided to help Dean dig up a new case.

The hunter had been suffering what he called 'cabin fever', which apparently meant that he had been stuck in the bunker far too long. He said the only cure was a new case, and since Castiel was looking for a distraction he decided to help. It didn't take them long to find a good enough lead, and they decided to head out bright and early the next morning.

Castiel spent the night researching the area that they believed to be haunted. Then he researched the violent deaths. He proceeded to even research the graveyards in the town. The angel looked at everything he could find, and still felt he wasn't distracted enough.

It was very early when Dean came grumbling out of his room to make coffee. Castiel followed the hunter into the kitchen hoping the other man's presence would help to distract him. It didn't take nearly long enough for him to relay all the information he'd gathered, and it was hard to tell if the hunter was even paying attention. Dean was practically sleeping in his coffee cup.

"Alright, buddy. I get it. Research done. Why don't you make yourself useful and go wake Sammy." The hunter yawned immediately following the words.

"I'm not sure how to wake him. You always seem upset when I wake you."

"That's because you just stand over my bed and stare! It's creepy!" Dean exclaimed dramatically.

"Well, what do you suggest I do?" The angel asked sincerely. He honestly didn't know the protocol for waking someone up.

The smirk that crossed the hunter's face said he was not going to learn the proper way this time either.

"I have an idea."

Dean carried a large glass of water with him while he showed Castiel how to wake his brother. If he had known what the water was for, he may have done something to prevent it.

"Rise and shine, Sammy!" A look of utter glee crossed the eldest Winchester's face as he upended the cup directly over his sleeping brother. Dean seemed to be aiming for the hair, but the younger brother was able to move his head after only a moment and the rest fell across his chest.

Sam rolled out of the bed as soon as he was awake enough to perform the feat, which was only seconds later. He landed on his feet with a glare for his brother.

"Seriously, Dean?" He grumbled as he tried to wipe some of the water from his skin, and squeeze the water from his hair. "What are you, five?"

"Cas and I found a case. Let's get the hell out of here." Dean didn't seem at all bothered by the hateful look his brother was sending him.

Castiel found it very difficult to pay attention to much more than Sam's nearly naked body. He was wearing only his boxers, and even they were riding low on his hips. The angel's eyes were inexplicably drawn to a drop of water that was slowly working it's way between the other man's pectorals, before moving swiftly to the line of hair at his navel. The sight was entrancing, and it took him a moment to realize these were the exact feelings he was supposed to be trying to avoid. He steeled his resolve to turn away from the sight, but before he could Sam moved.

The hunter lifted one arm into a stretch as he yawned, pulling the muscles of his torso tight and making them ripple a little as his arm lowered. Castiel's attention was immediately claimed again. He watched as the hunter rolled his shoulders and leaned back a little to complete the stretch.

"Well, that's just ridiculous." It took the angel a moment to realize the words had not been in his own head. The twin looks of confusion he received proved it, and he took that as his cue to get out of there as fast as he could. His plan to ignore his feelings again fell to pieces on Sam's bedroom floor. The chances of that sight leaving his head anytime soon were nonexistent.


	3. Last Resort

Having exhausted all other avenues of his research Castiel decided it was time to do the unthinkable. He'd have to ask Dean.

It wasn't that he didn't believe the hunter would be able to help him. He knew the eldest Winchester was actually known for the ease with which he could earn the affections of others. Castiel was more worried about Dean gaining the knowledge of what the angel was trying to do. The hunter was well known for being overprotective of his little brother at the best of times, and he didn't want to know what Dean would think of his feelings. Castiel would have to get the information out of the hunter without letting him know what the information was for.

The hardest part of all of his plans so far had been separating the brothers so he'd be able to talk to one of them without the knowledge of the other. He'd never really noticed before this adventure how much of their time was spent together. Nearly the only times he'd been able to speak to Sam alone had been if Dean had left for the night. He didn't really know how to get Dean alone.

Opportunity presented itself when the Winchesters were working out their grocery shopping lists. It was fairly clear that the brothers hated doing mundane things like that. They worked on a list for a few days before they would leave, making sure that nothing would be forgotten and they could get in and out quickly.

Normally the boys would do a chore like this together, but one word from Castiel about needing to speak to Dean and Sam was reluctantly offering to do the shopping alone.

As soon as the door was closed behind his brother, Dean's face split into a smile.

"Thanks, buddy! I hate grocery shopping."

The angel frowned. "I truly did wish to speak with you." He informed him, worried that Dean was going to try to slip away.

"Oh, I know. It's cool, we'll talk. I'm just so greatful to get out of doing that!" The hunter chuckled and clapped a hand to Castiel's shoulder, steering him in the direction of the library.

Once they were seated Dean prompted him to get on with it.

"So, what's on your mind?"

The hunter's face looked friendly, and curious. There was nothing to indicate that this conversation wouldn't turn out well. It didn't matter. The angel could feel his stomach turn in knots as he tried to think of what to say.

"Ever since I was human…" Castiel trailed off, not really knowing how to explain the emotions he'd been plagued with. He tried again. "When I was a human, I had to experience things I never had to before. Most pointedly, human emotions. There were so many, and they came all at once. I didn't know how to handle them, so I tried to just push them aside, and ignore them. It worked fairly well, and by the time my grace was returned I had a decent handle on them, or so I had thought. I believed that the return of my grace would be able to save me from my feelings."

Dean was beginning to look concerned, which was actually an expected reaction. The hunter hated talking about his feelings and was probably wondering why Castiel would have come to him with this. "Okay…?"

"Most of the more… overwhelming feelings have faded, but there is one feeling I have yet to rid myself of. I have been trying to ignore the feeling, but it won't go away. I was hoping that you might be able to help me figure this out."

The hunter's eyes widened and he looked almost spooked. "Uh… what kind of feelings are you having?"

"I feel an… attraction, and no matter what I do, or how I try to ignore it, it will not go away. I have given in, and I would like you to tell me how to go about revealing my feelings to the object of my affections."

Dean let out an explosive rush of breath that ended on a chuckle.

"Oh thank God! I was starting to get really worried there for a minute. I had no idea where you were going with this, and I thought I was going to have to pretend like I knew how to deal with human emotions. This feeling I know how to deal with." The hunter actually seemed pleased to be able to share his knowledge with the angel.

"So you've got yourself a crush, huh?" Dean grinned at Castiel in a way that made him feel he was being made fun of.

"I suppose." The angel tried to remember how to define a crush from his research. He believed it was comparable to infatuation. That would work. "Yes. I have a crush ."

The hunter chuckled, but probably only at the way he had accidently stressed that last word so oddly, though. "So you need me to tell you how to pick up women?"

Castiel paused before answering. He would like to correct the hunter. He wanted to make it clear that the person he was trying to 'pick up' was male, in case that mattered, but he was aware that the less Dean knew, the better. So, instead he nodded his agreement.

"Well, what kind of girl are we dealing with here? Different girls will need different approaches."

Castiel nodded his agreement again. That made sense. Certainly someone that was trying to get his attention would have to do it differently than if they were trying to get Dean's attention.

"So, what's she like?" Dean looked very interested in finding out what kind of girl had caught his attention.

Castiel had to take a moment before answering that question. How could he even describe the object of his affections?

"Well, is she good looking? Are all the other angels trying to get their hands on her too?"

The angel had to contain his reaction to that question. Yes, there were plenty of angels interested in Sam, but for very different reasons.

"Yes." He answered plainly, not bothering to elaborate.

"Well, that will make it a little more difficult. It's always harder when there are other dudes trying to get in your way." Dean seemed to contemplate the next question for a while before he spoke again.

"What kinds of things does she like to do? Maybe we can find something in common that will give you an in."

Castiel had, of course, already tried this tactic. He needed to at least try to give Dean something to work with, though. He had to force the pronoun out, and hoped that the hunter didn't notice.

"She likes to read."

Dean's face scrunched up dramatically. "Oh, no. She's smart?"

Not really knowing what that might have to do with anything, Castiel just confirmed the hunter's suspicions. "Yes. Is that a problem?"

"Well, no. Not really. It's just… the smart ones that are also pretty tend to be the hardest ones to get. They spend too much time trying to get people to realize that they are more than just a pretty face. It seems to make them kind of bitter about getting asked out." Dean leaned back in his chair, head falling back so he could stare at the ceiling. "This will certainly be a challenge."

Castiel hadn't really considered that Sam's intelligence would work against his plans.

"You should probably try to figure out what she's interested in. It'll be easier to make her feel like you respect her intelligence if you can talk to her about it. It's going to take time too. You couldn't have picked an easy one." Dean shook his head as if his picking one that wasn't easy was a bad choice, but thinking of all of his failed attempts to capture Sam's attention had the angel immediately agreeing to that assessment. It would certainly not be easy.

It was a week later before Castiel tried to speak to Dean about his feelings again. The first bit of advice had worked out quite well. Every time Sam figured out something that no one else had been able to, the angel had been there to make sure the hunter knew how much his intelligence was valued. At first, Sam had seemed surprised by the extra effort, but by the third time he'd done it Sam had actually blushed at the attention, with a quiet "Thanks, Cas" and a shy smile that melted the heart of the angel.

Clearly Dean's advice was leading him in the right direction, so he decided it was time to move to the next step.

"I believe I have convinced her that I respect her intelligence. What shall I do now?"

Dean's head popped up from the laptop he'd been staring intently at, and he glanced around the room as if the angel might have been talking to someone else.

"Dude. I told you. You've got to start conversations better. You can't just plop down and start talking."

Castiel considered Dean for a moment. "So, get this…" He said, causing the hunter to crack a smile.

"See! That's all I need." The hunter nodded, closing his laptop to give the angel his full attention.

"I have completed the first step. I need to know what to do next."

Dean's eyebrows shot to his hairline. "What makes you think the first step is completed?"

Castiel sighed and told him of his observations, carefully making sure to use the correct pronoun.

"She blushed? That's awesome! Nice work. Wow, you move pretty quick!" Dean seemed pretty impressed. It took a moment for the expression to fade. "I guess you've been going to see her while we're sleeping?"

A cold feeling of dread swept through the angel's vessel at the words. Of course Dean would have noticed that he hadn't left the bunker in days. Castiel hadn't thought about that. He quickly nodded in agreement with the explanation Dean had already come up with for him. He didn't enjoy lying to the Winchesters, but he was not ready for Dean to know what he was doing yet.

"I guess the next thing I would do is bring her gifts. And I'm not talking flowers and chocolate like they do in the movies." The hunter rolled his eyes as he said it, clearly indicating that he thought those gifts were foolish. "You want to ease her into the idea, so you don't want to do anything too revealing. If she likes reading, maybe you can let her borrow a book you know she'd be interested in. Even if you have to go buy the book before you can let her borrow it."

Dean paused as if waiting for confirmation that Castiel understood what he was insinuating. The angel nodded along. It was one of those things that humans called a 'white lie'. A harmless half-truth that they seemed to think was acceptable.

"Make sure you find other ways to compliment her. Now that she knows that you are interested in her mind first, she'll be much more likely to accept other compliments too."

This was one of the other things Castiel had read in his research. Complimenting people was supposed to be a way into their heart. He had decided it was one of the suggestions that had no real merit, but now that Dean was also saying it he'd have to rethink that.

"Don't go crazy with the compliments. You have to be a bit subtle about it still. Just tell her that her hair looks nice today, or that her shirt brings out the color of her eyes, or something. Don't go writing sonnets about her or anything." The hunter gave Castiel a look that said he was very serious about that part.

"I don't believe I am creative enough to do something like that anyway." The angel reassured his friend. "Thank you, Dean."

Castiel received a nod and a smile in response before he was ignored again in favor of whatever Dean was doing on his laptop.

In the following two weeks Castiel worked on using Dean's advice to get closer to Sam. He had taken to making sure that the hunter's coffee cup was always full. He'd studied the hunters as they set the machine to make their coffee, and had even begun making another pot when it was low. He'd then pour another warmer cup and exchange it for the one Sam had been drinking. The hunter had begun gracing him with a grateful smile when he would reach forward to take a sip of cold coffee and found it to be warm and satisfying instead.

It wasn't long before Dean started looking suspicious of his actions. Before the elder hunter could become too dubious Castiel decided to start bringing the pot of coffee with him to refill Dean's cup as well. It seemed to quell his mistrust.

The angel tried to think of other gifts to give Sam that wouldn't cause too much fuss, and his next stroke of genius had been vegetables. He knew the hunter had a hard time finding fresh vegetables at the local grocery, and tended to make an unhappy face as he looked at his choices. Although the plan to make Sam comfort food had fallen through, he realized he could still get the hunter some foods that might make him happy.

Castiel searched for a nearby farm, and struck a deal with the owner. He would make some much needed rain for the area, if the farmer would provide him with a variety of fresh vegetables. Of course the man agreed, although he clearly didn't believe that Castiel was truly an angel.

A wet half hour storm over a small section of Kansas later and the angel was laden down with multiple pieces of each of the vegetables that the farmer grew. He graciously accepted his gifts and thanked the farmer even as the man begged forgiveness for his disbelief.

When Castiel returned to the bunker with his overflowing boxes, he tried to make it seem perfectly normal for an angel to show up with vegetables for his charges. Sam was overjoyed when he saw the variety and quality of the produce, although Dean was beginning to look suspicious again. Castiel tried to pretend that he didn't notice. He didn't know how to explain his actions without giving himself away completely.

He had even found ways to complement Sam without being too obvious. He was actually fairly proud of the ways he'd come up with to tell the hunter how attractive he was without saying it outright. Knowing he was pushing his luck already with Dean, he always made sure the elder hunter was outside of hearing range before he showered attention on the object of his affections.

There was one question Castiel wanted to ask, that he was honestly a little afraid to. He knew that Dean wasn't big on talking about his feelings, and he was already lucky that the hunter had been as helpful as he was so far. By the time he had an opportunity to talk to Dean again, he'd worked up the courage to go ahead and ask it.

"How do you know if you are in love?"

Dean looked startled by the question, but his surprise quickly faded into that wary expression that he'd taken to wearing.

"I don't know, buddy. What did the internet say?"

"An intense feeling of affection for someone. A deep romantic or sexual attachment to someone." The angel answered immediately.

"Those are literal definitions. Did you read anything else about it?"

"The ways that people said they knew they were in love were very strange. Like they missed the person when they were not around. I feel as though there are multiple people that I could say that about. Some said that they couldn't eat or sleep when things were not going well with the one they loved. I never eat nor do I sleep, so I wouldn't be able to use that to tell."

The hunter's eyes held a deeper suspicion at that. He stared intently for a moment before seemingly ignoring the angel's questions completely.

"Do you think you're ready for the next step?" Apparently Dean didn't want to talk about love. Castiel allowed the subject change, although he still had questions on the subject and he really didn't have anyone else to ask about it.

"Yes. I believe that my gifts have been well received. What should I do now?"

"You're going to have to gather your courage for this one, buddy. Now that's you've got her all buttered up it's time to pop the question." The hunter's gaze was shrewd and the angel feared that he was being led astray at this point. It was very hard to understand the hunter's sense of humor at times.

"What question?"

"Well, it's time for you to ask her out! You've gotten close to her, so now all that's left is finding out if she's interested. You don't want to put a lot of time and effort into someone that's not interested at all." Dean's expression had faded back into that knowledgeable look he'd been using the other times they had talked on the subject, which eased the angel's hesitation.

"What should I ask?"

"I'd usually tell you to ask her to dinner, but you don't eat. Maybe see if she'd like to see a movie. Have you ever been bowling? Maybe you could do that." The hunter seemed genuinely interested in helping him find somewhere to take his date.

"I've never been bowling before. It doesn't seem very difficult though."

"Well, girls don't really like it when you beat them really badly at something anyway, so maybe you could give that a shot. Just make sure she knows that you've never played before. You don't want her to lose all respect for you if she beats you really bad."

It had been nearly a week of trying to get Sam alone before Castiel had finally had a chance, although Dean was only in his room and was very likely to come out at some point during the conversation. The angel only hoped that it wasn't until he had his answer.

"Sam, I've been wondering… would you like to go somewhere with me?"

The hunter's head popped up from the book he'd been absorbing. He looked intrigued by the question.

"Where did you want to go?"

Luckily Dean had given him some ideas about this.

"I would like to go bowling. I've never been bowling before."

Unluckily, Dean chose that exact moment to walk into the library. He paused just inside the door, glancing between them both. It took only a moment for him to realize the reality of the situation.

"You're hitting on Sam? Dude! I knew it!" Dean was huffing a bit dramatically and waving a hand to indicate the angel. "I wasn't really convinced until those damn vegetables, but I freaking knew it. I can't believe you got me to help you. I thought you were talking about doing a little cloud seeding, not hitting on my brother!" Dean glared at him, making it quite clear how unhappy he was to find out his advice had been used to get to Sam.

"You're hitting on me?" The youngest Winchester was clearly surprised by this new information. He also seemed unconvinced that was what was actually happening. Castiel had a hard time meeting his eyes..

"Yes…" The angel trailed off, not knowing how else to answer.

"Oh my God! This is what all this has been about this whole time?" Dean seemed to be pretty upset by the revelation. "Those searches on my laptop about physical attraction? You've got the hots for Sammy?" The hunter's voice had raised in a combination of panic and disbelief.

Castiel refused to answer, glaring hard at the floor and trying to pretend he was anywhere else. There was a long moment of silence as it became clear that the angel had no desire to reply.

"Is this what all your talk of emotions has been about?" The hunter's tone settled into a kind of forced calm.

Castiel couldn't think of a reason not to answer that question, so he did. "Yes."

"And what did you learn?"

The angel tried to think of a way out. He hadn't really expected to have to discuss his feelings today. It seemed he had already messed things up so badly that it was probably useless to keep trying to avoid the conversation. "It's hard to say, as I have never experienced these feelings before."

The look on Dean's face said he was not satisfied with that answer. When Castiel looked to Sam to see his reaction, the other hunter only continued to look surprised and confused.

"I do feel… a physical attraction." The angel could feel his face heating at the admission. He was also aware that it would only get worse.

"So, you decided to seduce him?" Dean seemed angry in that protective way he got when he was talking about his brother. Sam was clearly becoming more uncomfortable with the way the conversation was going. At least he was glaring at his brother and not Castiel. The angel probably would not have been able to answer with the younger Winchester's eyes on him.

"I don't posses the skills necessary to do such a thing."

That comment seemed to throw off Dean's argument, and his brows drew together in confusion. "So, what exactly was your endgame here?"

"What do you mean?"

"What were you hoping to get out of this if you didn't think you'd be able to seduce him?" Even though Dean still seemed a bit confused, he asked it in such an accusatory way it set the angel on edge.

"I don't know!" Even Castiel was surprised by his own emotional outburst. "I don't have any idea what I am doing! I've never experienced these feelings before. I have no idea what I'm meant to do with them." The angel tried to calm the emotions coursing through his veins. Before he could, Sam asked a question.

"But why me?" The hunter's voice was soft and curious, but Castiel still had too many uncontrolled emotions and he reacted without thinking.

"This is not my fault! You're a work of art! And you are never wearing a shirt! You did this to me!" His tone was unnecessarily accusatory and he regretted it immediately.

Sam was clearly startled by the outburst, but had the good grace to look ashamed. "I'm sorry, Cas. I didn't realize I was making you uncomfortable."

"You weren't making me uncomfortable." The angel comforted automatically, before he felt a heat rush to his cheeks. "I mean, yes. I suppose... I was a bit uncomfortable." He didn't bother to mention that the discomfort he'd gotten from seeing Sam shirtless had mostly been within his own pants. The sentiment seemed to come across anyway as the younger brother blushed and the elder made gagging noises.

There was a brief silence as they all seemed to gather themselves, then Dean started on him again. This time he seemed a bit resigned, though.

"Seriously, man. You have to know that it would be much easier if you went after someone else. It seems like with the amount of time you have hung out with us you should've caught on by now that you don't sleep with the people you're close to. Why didn't you just tell us so we could take you to a bar? It might be a little weird helping you pick up dudes, but we would have done it." Dean actually sounded sincere, which warmed the angel's heart. He knew that the hunter would be incredibly uncomfortable with something like that, and the thought that Dean would help him out anyway was a very nice one.

"I do understand, and I do appreciate the offer." Castiel took a deep breath and steeled himself. "But I don't want anyone else." He was well aware that the statement was very revealing, and he knew it wouldn't be lost on either of the hunters.

He watched as the comment sunk in. Both hunter's eyes widened, and when Sam leaned forward to rest his arms on the table he managed to knock his empty mug to the floor with a loud clank. Neither of them took their eyes off the angel, though. The silence that filled the room was deafening.

"Me?" Sam asked in what could only be described as disbelief.

"Yes." Castiel answered plainly. There was no point in hiding anymore. They already knew the truth; they were only having a hard time absorbing it.

"I don't understand." Sam had barely spoken during the conversation, and the angel was glad he was finally participating. It was a conversation he'd planned to have with only the younger Winchester to begin with. Although having Dean present had been mostly unavoidable.

The younger hunter continued, "Dean told me that you started experiencing emotions after you lost your grace. I get that you're still having a hard time controlling them... but he's the one that you share a more profound bond with. Why me?"

"I find that I would like to share more than just a profound bond with you."

The snort that issued from the eldest hunter at his words caused Sam's attention to swing his direction. Sam glared at his brother while Dean made hand gestures that Castiel didn't understand.

"Shut up, Dean." The younger hunter rolled his eyes as he turned his attention back to the angel. Dean hadn't said anything, but Castiel understood that the Winchesters seemed to have their own language sometimes, so he ignored it.

"Wait, wait, wait." Something seemed to occur to Dean at that moment and he paused his motions. "That's what those love questions were about? You think you're in love with Sam?"

Castiel averted his gaze before he answered. "I can't be sure as I've never felt that emotion before. I can only go on what I have learned."

There was a pause before Dean seemed to lose patience. "And?"

The feelings overwhelming the angel as he spoke were a mixture of fear and hope and some other less definable emotions. The fear nearly kept him from answering, but he had always been a soldier and he felt it was too late to back down now. He forced his eyes to meet Sam's. "Yes." His voice came out barely audible, but it carried in the quiet anyway.

The silence stretched for a minute until Dean finally broke it by moving. A happy smile split the hunter's face, and he clapped a hand on the angel's shoulder as he passed him, heading back toward the hallway. "Well, Sammy's been in love with you for ages, so I guess it'll all work out."

Castiel couldn't help the shock that crossed his face, and he turned his attention back to Sam. The hunter's face may have looked even more shocked than his own, and he stared at the doorway his brother had just exited through.

It took Sam a while to compose himself again, and by the time the hunter turned his attention back to him, the angel had been able to collect himself as well. He knew not to put much stock into some of the things Dean said. The elder hunter liked to make jokes.

"Listen, Cas..."

"It's fine. I don't expect you to return my feelings, Sam. I understand if that is not something that you are willing to do. My vessel is male, and I know that it can be hard for humans to accept the idea of a mate of the same sex. I had hoped that you would at least allow me the chance to try to earn your affections."

Sam huffed a laugh at that and finally met his eyes. "And then what? Hope the gay rubs off?" Even as his words were unsettling, his tone was kind. As it usually was.

"We don't have to have a physical relationship. I am perfectly capable of keeping my hands to myself, as they say. I only hoped that I could become closer to you."

The hunter rose from his seat and slowly made his way around the table between them.

"Are you sure about that? Isn't it my fault that you are stuck with all these emotions in the first place?" Sam was suddenly right in front of the angel, but before Castiel could react, the hunter leaned back slightly to prop himself against the table.

Castiel blushed, from his nearness and his words. "I didn't actually mean that." He admitted.

The hunter's smile was fond as he accepted the half-apology. "I know." Sam rubbed his palms across the front of his jeans in a gesture of nerves that even the angel recognized.

"So, how did you want to go about 'trying to earn my affections'?"

"Perhaps we can start with a date? Dean said that is what normal people do when they are interested in someone." Castiel said cautiously.

Sam huffed another laugh at that. "Okay. I think we can start with a date. But after this, no more plays from Dean's book of getting laid. I don't even want to know what he thinks step number two is."

"Alright." The angel agreed immediately, and was surprised by the happiness that shot through him at the idea.

"Besides, if that last comment he made was any indication, he's not upset that you were trying to hit on me. He was upset that he was unknowingly giving you advice on how to do it. It's probably a good idea to keep him out of it." The hunter sent him that boyish grin that made the angel's heart beat faster and he reached out toward Castiel's hand.

"That's good." He said, trying not to show how much the other man was affecting him. Although he brought his own hand forward to meet the other.

The calluses on the hunter's fingers rubbed pleasantly against his skin as their hands slotted together. Sam's was larger than his vessel's, almost dwarfing it. It was a sight that appealed to the angel in a way he couldn't define. When the hunter's thumb wrapped around to rub gentle in circles on the back of his hand a shot of pleasure rolled down his spine, unexpectedly.

"Cas." The angel realized his eyes were fixed on where Sam's hand was gently caressing his own and they snapped up to meet the hunter's.

"I'm just going to come right out and say this, because I know that subtlety goes right over your head."

Castiel nodded, he knew that it was true.

"You're not going to have to work very hard to earn my affections, because you already have them. I suppose I haven't been very good at hiding it if Dean already knew." The angel was graced with another shy smile, and his heart seemed to stop in his chest this time. It started again at a very quickened pace as the hunter's eyes seemed to sweep the entirety of his vessel. Sam's smile turned impish. " And I seriously doubt that physical compatibility will be a problem."


End file.
